The present invention relates to multifunctional water-soluble cross-linked cationic terpolymers and personal care compositions comprising these multifunctional water-soluble cross-linked cationic terpolymers. The present invention also relates to methods for using such cationic terpolymers to treat various substrates; for example, hair, skin, etc.
Cationic polymers have been used extensively in water treatment, paper making, mineral processing, petroleum recovery, textile dyeing, cosmetics and pharmaceuticals. Among the most important and extensively used cationic polymers are the quaternary ammonium polymers of diallyldimethylammonium chloride (DADMAC). These polymers are also known to be used in personal care applications.
Polymerization of DADMAC is typically carried out in aqueous solution using a free radical initiator such as a persulfate salt. Several approaches have been tried to increase the molecular weight of DADMAC polymers, including polymerization with added inorganic salts, polymerization in oil-in-water emulsions or suspended droplets, and addition of cross-linkers during polymerization. These methods are well known to those skilled in the art.
U.S. Pat. No. 3,968,037 discloses that cationic polymers made by inverse emulsion polymerization with cross-linking and branching agents are used as flocculants and for the treatment of activated sewage sludge.
Cationic polymers have been used extensively in home and personal care, water treatment, papermaking, mineral processing, petroleum recovery, fabrics, and pharmaceuticals. Among the most important and extensively used cationic polymers are the quaternary ammonium polymers of diallyldialkyl ammonium compounds. In fact, homopolymers of diallyldimethyl ammonium chloride (DADMAC) are well known in the home and personal care industry as polyquaternium 6, and are used extensively in skin and hair care applications.
The use of homo- and copolymers of diallyldimethylammonium salts in personal care applications has been disclosed in several U.S. patents.
The present invention relates to novel water-soluble, cross-linked, and cationic terpolymers, for example of diallyidimethylammonium chloride (DADMAC) and diallylamine (DAA), that provide excellent conditioning properties. The terpolymers of this present invention provide the extra conditioning benefits required in a personal care product. They also contribute useful properties to skin care products.
U.S. Pat. Nos. 3,700,623 and 3,833,531 teach making certain acid stabilized poly(diallylamine)-epihalohydrin resins, the disclosure of which is herein incorporated by reference. The obtained resin had a tendency to gel on standing. The resin solution was therefore stabilized against gelation by adding enough water-soluble acid (e.g. HCl) to adjust the pH to about 2. The acid-stabilized poly(diallylamine)-epichlorohydrin resins were reactivated prior to use by addition of a base (e.g. NaOH) to adjust pH to above 7. The half-reacted epihalohydrin entities of the alkaline curing resins impart epoxy functionality for crosslinking reactions after being reactivated by addition of alkaline base prior to use. These polymers are insoluble after crosslinking.
U.S. Pat. Nos. 4,354,006, 4,419,498 and 4,419,500 teach a process for making certain poly(DAA-ECH) polymers by reacting a diallylamine (DAA) polymer first with an allyl halide and then with hypohalous acid to convert the allyl substituents to halohydrin moieties, the disclosures of which are herein incorporated by reference.
JP 6,108,382 discloses another way to make certain poly(diallylamine)-epihalohydrin polymers. A diallylamine-epihalohydrin halo salt monomer is first prepared by reacting diallylamine with an epihalohydrin (typically epichlorohydrin, ECH) and then neutralizing with a halo acid (typically HCl).
U.S. Pat. No. 5,147,411 discloses a method to prepare the DM-ECH monomers (3-halo-2-hydroxypropyl)diallylamine and (2,3-epoxypropyl)diallylamine, and their quaternary ammonium salts, the disclosure of which is herein incorporated by reference.
U.S. Pat. No. 4,341,887 discloses that the reaction product of diallylamine and epichlorohydrin (3-chloro-2-hydroxypropyl)diallylamine (a DAA-ECH monomer), can be converted to N,N-diallyl-3-hydroxy-azetidinium chloride (DM-ECH azetidinium monomer) by heating in the presence of water, the disclosure of which is herein incorporated by reference.
The above-reviewed patents involve use of an epihalohydrin as a reactive compound to react with DAA monomer or a DAA polymer. Since an epihalohydrin (e.g. epichlorohydrin) is a difunctional reactive crosslinker, highly crosslinked insoluble end products are obtained when fully reacted with equivalent high DAA-containing (i.e. >5%) polymers.
Commonly assigned U.S. Pat. No. 6,323,306, the disclosure of which is incorporated by reference, discloses a method to prepare certain water-soluble cationic polymers by reacting an amino-functionalized DADMAC polymer with a difunctional reactive crosslinker. The reactive crosslinkers include epihalohydrin and other polyfunctional compounds that can be used to cross-link the diallylamine polymers. The patent is limited to a DAA content of less than 5% to prevent formation of undesirable insoluble products which can be caused by excessive crosslinking due to use of the difunctional reactive crosslinker.
U.S. Pat. Nos. 3,912,808, 3,986,825, and U.S. Pat. No. 4,027,008 disclose DADMAC homopolymers and copolymers with acrylamide derivatives in hair care compositions, the disclosures of which are herein incorporated by reference.
U.S. Pat. Nos. 5,622,647 and 5,476,522 disclose DADMAC and vinyltrialkoxysilane copolymers for dewatering in the mining industry, the disclosures of which are herein incorporated by reference.
Copending U.S. application Ser. No. 11/595,152, filed on Nov. 9, 2006, discloses the preparation of functionalized cationic polymers and their application in personal care, the disclosure of which is herein incorporated by reference.
Copending U.S. Provisional Application No. 60/899,675, filed on Feb. 6, 2007, discloses the preparation of polysiloxane block copolymers, the disclosure of which is herein incorporated by reference.
U.S. Pat. Nos. 6,383,995, 6,432,894, 6,403,542, and 6,383,994 discloses compositions for washing keratin-based materials, the disclosures of which are herein incorporated by reference.
U.S. Pat. No. 6,383,996 discloses antidandruff compositions for treating the hair and scalp, the disclosure of which is herein incorporated by reference.
U.S. Pat. No. 6,383,993 discloses compositions for washing keratin-based materials comprising a cationic galactomannan gum and an acrylic terpolymer, the disclosure of which is herein incorporated by reference.
U.S. Pat. No. 6,926,900 discloses antidandruff compositions for treating the hair and scalp comprising an acrylic terpolymer, the disclosure of which is herein incorporated by reference.
U.S. Pat. No. 6,169,058 discloses compositions and methods for hydraulic fracturing, the disclosure of which is herein incorporated by reference.
U.S. Pat. No. 5,465,792 discloses methods of controlling production of excess water in oil and gas wells, the disclosure of which is herein incorporated by reference.
US 2004/0105832 discloses cosmetic compositions containing a fructan and a cationic polymer, the disclosure of which is herein incorporated by reference.
WO 2001/41719 discloses cosmetic compositions containing a quaternary silicon and a pearling agent.
Accordingly, there is still a need for water-soluble, cross-linked, and cationic terpolymers that provide excellent conditioning properties in personal care products. The cationic terpolymers of this present invention provide the extra conditioning benefits required in a personal care product. These cationic terpolymers also contribute useful properties to skin care products.